834-50-4

Basic information

• Product Name: Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester
• Synonyms: Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester;1-Ethoxycarbonylbicyclo[2.2.2]octane-4-carboxylic acid;4-(Ethoxycarbonyl)bicyclo-[2.2.2]octane-1-carboxylic acid;Bicyclo[2.2.2]octane-1,4-dicarboxylic acid 1-ethyl ester;NSC 177416
• CAS NO: 834-50-4
• Molecular Formula: C₁₂H₁₈O₄
• Molecular Weight: 226.26892
• Mol File: 834-50-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 336.8 °C at 760 mmHg
• Flash Point: 125.2 °C
• Appearance: /
• Density: 1.265g/cm³
• Vapor Pressure: 2.06E-05mmHg at 25°C
• Refractive Index: 1.543
• CAS DataBase Reference: Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester(834-50-4)
• EPA Substance Registry System: Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester(834-50-4)

Safety Data

• Hazardous Substances Data: 834-50-4(Hazardous Substances Data)

Usage

General Description

Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester is a chemical compound that is used in the production of various industrial and commercial products. It is often used as a building block in the synthesis of pharmaceuticals, agrochemicals, and advanced materials. Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester is a monoethyl ester, meaning it has an ethyl group attached to one of the carboxylic acid functional groups. It has a unique bicyclic structure, which gives it specific properties that are useful in a variety of applications. Overall, this chemical compound is valuable in the field of organic synthesis and has a wide range of potential uses in the manufacturing of various products.

InChI:InChI=1/C12H18O4/c1-2-16-10(15)12-6-3-11(4-7-12,5-8-12)9(13)14/h2-8H2,1H3,(H,13,14)

Upstream product

• 1659-75-2 Bicyclo<2.2.2.>octan-1,4-dicarbonsauere-ethylester 
• 41034-55-3 (+/-)-dispiro[[1,3]dithiane-2,2'-bicyclo[2.2.2]octane-5',2''-[1,3]dithiane]-1',4'-dicarboxylic acid diethyl ester 
• 787-07-5 diethyl 1,4-cyclohexanedione-2,5-dicarboxylate 
• 1686-98-2 2,5-Bis-ethylendimercapto-bicyclo<2,2,2>octan-1,4-dicarbonsaeure-diethylester 
• 843-59-4 Diethyl 2,5-Dioxobicyclo<2.2.2>octane-1,4-dicarboxylate 

Downstream Products

• 79663-72-2 ethyl 1-(aminocarbonyl)bicyclo<2.2.2>octane-4-carboxylate 
• 444344-91-6 4-[[(benzyloxy)carbonyl]amino]-bicyclo[2.2.2]octane-1-carboxylic acid 
• 444344-90-5 ethyl 4-[[(benzyloxy)carbonyl]amino]-bicyclo[2.2.2]octane-1-carboxylate 
• 444344-93-8 N-(4-aminobicyclo[2.2.2]octane-1-carbonyl)-L-glutamic acid dimethyl ester 
• 444344-92-7 N-[4-[[(benzyloxy)carbonyl]amino]bicyclo[2.2.2]octane-1-carbonyl]-L-glutamic acid dimethyl ester 
• 444344-94-9 N-[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]bicyclo[2.2.2]octane-1-carbonyl]-L-glutamic acid dimethyl ester 
• 15941-09-0 4-cyanobicyclo<2.2.2>octane-1-carboxylic acid 
• 788-71-6 4-ethoxycarbonylamino-bicyclo[2.2.2]octane-1-carboxylic acid ethyl ester 
• 13595-17-0 4-amino-bicyclo[2.2.2]octane-1-carboxylic acid 
• 54829-94-6 4-cyano-bicyclo[2.2.2]octane-1-carboxylic acid ethyl ester 
• 1299425-88-9 ethyl 4-iodobicyclo[2.2.2]octane-1-carboxylate 
• 905457-33-2 4-iodo-N-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-N-(pyridin-2-yl)bicyclo[ 2.2.2]octane-1-carboxamide 
• 1299426-08-6 4-iodo-N-(2-(4-(2-hydroxyphenyl)piperazin-1-yl)ethyl)-N-(pyridin-2-yl)bicyclo[ 2.2.2]octane-1-carboxamide 
• 80745-61-5 4-iodobicyclo<2.2.2>octane-1-carboxylic acid 

Relevant articles and documents

Design, synthesis, radiolabeling, and in vitro and in vivo evaluation of bridgehead iodinated analogues of N -{2-[4-(2-methoxyphenyl)piperazin-1-yl] ethyl}- N -(pyridin-2-yl)cyclohexanecarboxamide (WAY-100635) as potential SPECT ligands for the 5-HT1A receptor

Here we describe the design, synthesis, and pharmacological profile of 5-HT1A receptor ligands related to 1 (WAY-100635). The cyclohexyl moiety in 1 and its O-desmethylated analogue 3 were replaced by the bridgehead iodinated bridge-fused rings: adamantyl, cubyl, bicyclo[2.2.2]octyl, or bicyclo[2.2.1]heptyl. All analogues displayed a (sub)nanomolar affinity for the 5-HT1A receptor in vitro. Compounds 6b and 7b appeared to be selective for this receptor over other relevant receptors and could easily be iodinated with radioactive iodine-123. In humane hepatocytes, [ 123I]6b showed a low propensity for amide hydrolysis and a stable carbon-iodine bond. The biodistribution of [123I]6b and [ 123I]7b in rats revealed that the carbon-iodine bond was also stable in vivo. Unfortunately, the brain uptake and the specificity for both radioligands were significantly lower than those of the parent molecule 1. In conclusion, the designed tracers are not suitable for SPECT imaging.